Getting into Y Combinator, on very little sleep
When Solomon called to tell me we were in Y Combinator, I was alone in San Francisco. Giuseppe had already left. I had spent the day walking around the city, after a night spent answering questions about our company. By then I had been awake for most of two days.
I have a photograph of myself raising a fist on a video call with the team. The grin is enormous. I remember the relief almost physically: we had got in.
The story had started a few weeks earlier, in my kitchen in Rome, at four in the morning. Our first YC video interview was on California time. I made two coffees and tried to get my brain into a state where it could explain a company in English.
Then came the invitation to interview in person. Giuseppe and I booked the flight: Rome, Munich, San Francisco. The Munich stop involved beer, pretzels and white sausages. There are worse ways to break a journey.
We arrived around Halloween and stayed in a tiny Airbnb in Redwood City. Nearby was Donut King. I remember the shop almost as clearly as the YC office: the crown on the window, the trays of glazed doughnuts, the completely unreasonable quantity of sugar. Our California headquarters had excellent access to doughnuts.
Our interview was on 5 November 2018, at 12:15 pm Pacific time. Adora Cheung, Solomon Hykes and Dalton Caldwell were in the room. Giuseppe was beside me. Solomon had founded Docker; these were people whose work we knew, and whose judgement suddenly mattered a great deal to our immediate future.
They asked about everything. The product, the business, the customers, the numbers. We were building Askdata so people could ask questions of their business data in ordinary language. That idea connected a lot of things we had seen in companies: data everywhere, access concentrated in a few technical hands, people waiting for answers to fairly simple questions.
Explaining the breadth of it was difficult. AI did not automatically make a company exciting in those conversations. Even at YC, I felt we struggled to get across why a horizontal platform could support so many different use cases. To us, those uses belonged together. To someone meeting us for the first time, they could sound like several businesses competing for our attention.
There was a fair question underneath that difficulty: where would somebody actually start using it? We had to make the opportunity understandable without spending the whole interview listing everything the technology might eventually do. I knew the problem well. Compressing that knowledge into answers under pressure was another skill entirely.
After the interview, we waited. There is a photo of Giuseppe and me at Pier 39 that evening, still in our INNAAS clothes. We are smiling. I was also running through the interview in my head.
Later, Solomon wrote with more questions. We had talked about financial traction; he wanted the evidence. The follow-up was detailed and specific. We needed to put the numbers, documents and explanations together properly.
We worked through the night, and the exchange continued the next day. One of my favourite photographs from the trip catches Giuseppe watching television while I was working on the reply. There is a business show on the screen. He appears to be having a rather more relaxed investment discussion than I was.
Giuseppe, television, and our very small Airbnb. I was working on Solomon’s questions.
The waiting was worse than the interview. In the room, at least I could answer. Afterwards, every unanswered question acquired several possible meanings. Was this serious interest? A final check? A polite way to find the reason to say no? Exhaustion made me very good at generating explanations and very bad at choosing between them.
Giuseppe left San Francisco. I stayed and walked. I walked for much of the day, carrying the same question around a very large city. There was nothing particularly strategic about it. I had energy from the anxiety and almost none from sleep.
On the evening of 6 November, Solomon called. He told me we had been accepted into the Winter 2019 batch. The acceptance email followed that evening, at 6:48 pm California time.
I shared the news with the team over video. That is where the raised fist comes from. We had brought the company this far together, and I wanted them to have the moment with me, even through a screen.
My celebration in San Francisco was fairly modest. I had a drink, then found somewhere that was still serving food: Schroeder’s. At that point it felt like the last open restaurant in the city. I ate a schnitzel. After all the imagining of what getting into YC might feel like, the actual evening involved a very happy, very tired Italian eating German food alone in California.
Then I called an Uber and fell asleep in the car on the way home.
Two coffees in Rome, a flight through Munich, Donut King, an interview, a long night of financial questions, a day of walking, and finally that phone call. When I think about getting into YC, I can still feel how tired I was. I can also see that ridiculous grin on the video call.